Androstenone

Source: Wikipedia, the free encyclopedia.
Not to be confused with Androsterone, Androstenedione, or 5α-Androst-2-ene-17-one.

Androstenone
Skeletal formula of androstenone
Ball-and-stick model of the androstenone molecule
Names
IUPAC name
5α-Androst-16-en-3-one
Systematic IUPAC name
(3aS,3bR,5aS,9aS,9bS,11aR)-9a,11a-Dimethyl-3,3a,3b,4,5,5a,6,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.038.367 Edit this at Wikidata
UNII
  • InChI=1S/C19H28O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13,15-17H,4-8,10-12H2,1-2H3/t13-,15-,16-,17-,18-,19-/m0/s1 checkY
    Key: HFVMLYAGWXSTQI-QYXZOKGRSA-N checkY
  • InChI=1/C19H28O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13,15-17H,4-8,10-12H2,1-2H3/t13-,15-,16-,17-,18-,19-/m0/s1
    Key: HFVMLYAGWXSTQI-QYXZOKGRBP
SMILES
  • O=C4C[C@@H]3CC[C@@H]2[C@H](CC[C@@]1(/C=C\C[C@H]12)C)[C@@]3(C)CC4
Properties
C19H28O
Molar mass 272.432 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Androstenone (5α-androst-16-en-3-one) is a

in heat, results in the female assuming the mating stance. Androstenone is the active ingredient in 'Boarmate', a commercial product made by DuPont sold to pig farmers to test sows for timing of artificial insemination.[1][2][3][4][5]

Biosynthesis

Androstenone is

3-ketosteroid reductase.[6]

Properties

Depending upon the subject, androstenone can have an unpleasant, sweaty, urinous smell, a woody smell, or even a pleasant floral smell.[3][7][8]

There are two different genotypes that allow an individual to smell androstenone. The first genotype, which consists of two fully functional copies of the gene, is the RT/RT allele, and the second is the RT/WM allele.[citation needed] The OR7D4 receptor[4] has two non-synonymous single nucleotide polymorphisms,[9] which cause the gene to have two amino acid substitutions, which in turn cause the receptor to act differently. Those in possession of the two proper genes, (RT/RT) for OR7D4 tend to describe the odor for the steroid as the odor of stale urine. Those with only one gene (RT/WM) typically described the odor as weak or were not able to detect it. They can also find the smell 'pleasant', 'sweet' or 'similar to vanilla'.[10]

In small amounts, the odor is hardly detectable by most people. This may be due to a polymorphism in the receptor gene that codes for the androstenone receptor.[11] However, the ability to detect the odor varies greatly. It has been shown that the odor can be detected by people down to levels of 0.2 parts per billion to 0.2 parts in 100 million.[12] Several groups report, however, that some individuals who initially cannot smell androstenone can learn to smell it by repeated exposures to it.[13]

Detectability as a pheromone

In humans, androstenone also has been suggested to be a

better source needed] The vomeronasal organ is an auxiliary olfactory sense organ responsible for the detection of pheromones as more than just an odor. Most adult humans possess something resembling this organ, but there is no active function. Humans lack the sensory cells that exist in other mammals needed to detect pheromones beyond a smell.[clarification needed][dubious – discuss] Humans also lack the genetic ability to produce these sensory cells actively.[citation needed
]

There is also a specific anosmia to the odor in some humans; they are unable to smell specific odors, but have, otherwise, a normal sense of smell. However, this should, by no means, be regarded as indicative for being labeled as a pheromone, as it is true of over 80 olfactory compounds.[15]

To animals, the smell of androstenone can act as a social sign of dominance and can be a way of attracting a mate.[citation needed][dubious – discuss]

Commercial use

Some commercially available products are advertised using claims that they contain human sexual pheromones, including androstenone, and that they can act as an aphrodisiac.[citation needed]

See also

References

  1. PMID 15008668
    .
  2. PMID 8980852
    .
  3. ^
    PMID 2813372
    .
  4. ^
    PMID 6589634
    .
  5. PMID 22060698
    .
  6. hdl:2066/113615
    .
  7. ^ "Sniffers' genes dictate if sweat smells sweet". New Scientist. 19 September 2007.
  8. ^ Steenhuysen, Julie (16 September 2007). "Stinky? It's not his sweat, it's your nose". Reuters.
  9. S2CID 4417235
    .
  10. ^ Swaminathan, Nikhil (18 September 2007). "The Scent of a Man". Scientific American.
  11. PMID 16844768
    .
  12. ^ Birchall, Annabelle (25 August 1990). "A whiff of happiness: Can smelling a molecule contained in human sweat ease anxiety and stress? Some scientists think so, and argue that 'osmotherapy' may also help people to slim or stop smoking". New Scientist.
  13. ^ Graham, Sarah (23 October 2002). "Nostrils Share Information for Recognizing Scents". Scientific American.
  14. OCLC 63367504.{{cite book}}: CS1 maint: date and year (link
    )
  15. PMID 14678483
    .
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